Hydrochloric Acid → N6-(3-iodobenzyl)-2-Chloro-5'-O-methyladenosine

HRID 6668

Reaction equation

HRID 6668 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25][CH3:26])[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)=[C:4](Cl)[N:3]=1.[I:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH2:33].Cl>>[I:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH:33][C:4]1[C:5]2[N:6]=[CH:7][N:8]([C:9]=2[N:10]=[C:2]([Cl:1])[N:3]=1)[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][CH3:26])[C@@H:17]([OH:18])[C@H:12]1[OH:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 970123-IodobenzylamineHCID 110698082,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-beta-D-ribofuranosyl)-purine

Product 1

HCID 10896741N6-(3-iodobenzyl)-2-Chloro-5'-O-methyladenosine

Procedure

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (61, 372 mg, 0.89 mmol) and 3-iodobenzylamine.HCl (1.34 mmol, 360 mg). The mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2). Yield 383 mg (0.72 mmol, 81%), mp 84–86° C.; Rf 0.59 (10% MeOH in CH2Cl2). The product was recrystallised from CH3COCH3; 1H NMR (DMSO-d6) δ 8.89 (bs, 1H, NH), 8.35 (s, 1H, H-8), 7.73 (s, 1H, CCHCI), 7.60 (d, 1H, J=5.83 Hz, CCHCHCH), 7.33 (d, 1H, J=6.12 Hz, CCHCH), 7.12 (t, 1H, J=7.55 Hz, CCHCH), 5.82 (d, 1H, J=5.15 Hz, H-1′), 5.54 (d, 1H, J=5.84 Hz, OH-2′), 5.30 (d, 1H, J=5.49 Hz, OH-3′), 4.61–4.51 (m, 3H, NHCH2, H-2′), 4.09–4.00 (m, 2H, H-3′,4′), 3.56–3.52 (m, 2H, H-5′), 3.28 (s, 3H, OCH3); MS m/z 532 (M+H)−; Anal. (C18H19ClIN5O4.0.3 CH3COCH3) C, H, N.

Workup

  1. customThe mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2)
  2. customThe product was recrystallised from CH3COCH3

Sources & evidence

ORD record
ord-26f4648a589c472e97796c0f8fadc0ad
Source dataset
uspto-grants-2006_08
Patent number
US07084127B2

Linked notes

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